


Skating by Moonlight

by Moonstone_Plus



Category: Sydney to the Max (TV)
Genre: Anal Sex, Cock Slapping, Cock Tease, Cock Worship, Creampie, Dom/sub, Gay Sex, Group Sex, Large Cock, M/M, Oral Sex, Public Sex, Rough Oral Sex, Rough Sex, Semi-Public Sex, Sex, Skateboarding, Skater boy - Freeform, Spitroasting, Twinks, Underage Sex, Watching
Language: English
Status: Completed
Published: 2020-12-01
Updated: 2020-12-01
Packaged: 2021-03-10 00:21:05
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,113
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27815236
Author URL: https://archiveofourown.org/users/Moonstone_Plus/pseuds/Moonstone_Plus
Summary: Late night, Max has snuck out to once more try becoming a Dog Boy and serves to please Riccoli by any means necessary. being completely submissive to the older skater and the Dog Boys for the whole night.
Relationships: Max Reynolds/Riccoli
Comments: 2
Kudos: 12





	Skating by Moonlight

Thirteen-year-old Max Reynolds gulped a little as he stared at the skatepark, going against his best friend’s warning about going there alone at night to meet up with the Dog Boys. With Leo not trusting Riccoli and his group, and disliked how interested Max was in hanging with them over him. 

He didn’t care what Leo thought. These guys were cool, and only cool people had good futures, getting famous like Tony Hawk.

It looked different at night, illuminated by the dull glow of a street lamp overhead that cast long shadows in the deep half pipes and tall ramps. A little spooky in all honesty. But he wasn’t focusing on the park itself. Instead searching through the inky blackness, following the sound of wheels against the smooth stone until he caught a group of shadows on the other side. The Dog Boys already skating. Max wanted to impress them by skating down the darkened ramp ahead of him, but had to bail out and walk when he slipped.

The Dog Boys were swift on their boards. Moving through ramps with ease, like it was nothing. Only one stood out, looming over the group atop of the ramp. Riccoli himself.

“W-what’s up!” Max copied their greeting, his voice cracking.

“Yo. So you did come. Thought you’d be asleep already.” Riccoli smirked looking down on him. “Thought your mommy would have had you tucked into bed with a teddy, hours ago…”

“I snuck out!” Max said back. Shivering in the chill despite his black and red hoodie, with thumb holes for warmer palms. “And you told me to come… so I did!”

“Good, so you already know to listen…” Riccolli smirked. “That’s a good beginning…”

Max flashed him a painfully innocent smile, which had the other three Dog Boys snickering his way. He smiled at them too and gave a boyish wave, thinking of each as another friend and fellow Dog Boy. This only earnt him more amused looks and snickering from the trio.

“Sooo, are we going to skate or what?” Max grinned, excitement clear in his face. An invitation could only mean one thing for him. Skating all night long until he dropped dead tired.

“The or what is more accurate, Reynolds,” Riccolli smirked, as he lowered his board and skated down to the teen. He was much taller, and would have intimidated any other kid. Max just smiled. “Bring any food? The boys are starvin’!”

Looking around at them all, who now rubbed their tummies, Max slowly shook his head, then looked back to Riccoli.

“I, uh, didn’t know I should…” Max blushed.

“Duuuuuuuude, the newbie always brings food! How can you be a good dog and not bring food?” Riccoli scoffed, rolling his eyes at the young boy’s ignorance. Enjoying that Max was rather unphased by it all, and more concerned with being a good member of the group than anything. “Well since the puppy didn’t bring any food, the big dogs will just have to satisfy their hunger elsewise…”

“But, I just… arrived…” Max whispered the last words, trying to see if Riccoli was being serious.

Riccoli brushed his words off, shrugging off his jacket. “How old are you, Max?”

“Thirteen… perfect Dog Boys age right?”

“Sounds more like a puppy.”

Max blushed a little, luckily something unable to be seen by the older boys. “I-I’m not a puppy… I can be a full dog boy!”

“You’re a pup until I say so, Max. How about we make a deal?” The older blond suggested, and moved on before Max could even agree to the terms. “You do whatever I say, and you can be a full Dog Boy like us. First, you need to give me your hoodie. It’s sick.”

“N-No… I like this hoodie! I’m not giving it away!” Max protested, not wanting to give up one of his only cool hoodies.

Ricolli sighed at his group of friends, who all shook their heads in disappointment. “Guess he doesn’t want to be a Dog Boy…”

“I-I’m not giving you my hoodie…” Max muttered, holding onto his hoodie tight. The teen wondered if he should just go home now and accept that Leo was right.

“I didn’t say I want to wear it. Way too small,” Riccoli muttered. While deciding that he would need to go about this another way. The young pup wasn’t going to be giving away any clothes or his board. Much to the blonde’s annoyance since the hoodie was cool. “Fine. You said you’re, like, twelve right? Can you even cum yet?”

“Thirteen! And what does that have to do with skating!” Max asked, glad that the boy had given up on wanting his hoodie. His curiosity peaked. No other boy had ever talked about that before. It was too mature for him and Leo to bring up. And with his mother, saying anything of the sort at home was out of the question.

“All the Dog Boys can cum. I’ve got the biggest…” Riccoli answered vaguely. Noting that Max was hanging off every word.

Max’s eyes glanced down. “Biggest… what?”

“What do you think, pup? You should know the answer if you’re a Dog Boy material.” Riccoli smirked, noticing where the boy’s eyes went. Casually, he cupped his crotch and gave it a squeeze, then a little scratch before releasing it much to Max’s awe. Openly staring at it for a long moment. 

“Y-You have the biggest… that?” Max questioned, looking around at the other Dog Boys for semi-confirmation.

The others weren’t looking at them any more, busy skating around like a hungry circle of piranhas. Trapping him alone with Riccoli and his cocky attitude. 

“Funny. You think I’m talking about one thing,” The older boy laughed. Loving the way he made Max squirm and blush with submissive embarrassment. 

“W-well, how are you comparing… that?” Max asked, imagining if they all had seen each other or even wank together to be able to compare.

“Why do you care, huh pup? Bet yours is pretty small compared to mine, since you’re a little pup. You want to see it, don’t you?” Riccoli pushed, a grin plastered on his handsome face. In the darkness it was impossible to see but his loose shorts were tightening with a bulge.

“Of course!” Max exclaimed. Still feeling nervous, but curiosity quickly got to him.

“Hmm? Really want to?” Riccoli smirked. Anyone that remotely knew him could have guessed what was on his mind. A boy like Max, eager to do anything to please, would be perfect. He motioned for the young boy to approach while once more cupping himself for Max. “Come here and get on your knees, pup. I’ll show you why I'm top dog, and you’re the little pup.”

Max just nodded quickly as he approached him, his eyes on the prize the whole time. When their chests were all but touching, he kneeled down with a smile on his face. And for a moment this all seemed too easy, even for Riccoli. Until Max spoke.

“All guys do this, right? Like, it’s a friend thing!” His innocence warped his view on how mature friends talk about anything sexual. Riccoli and the Dog Boys barely held off laughing. “Showing their things and talking about the biggest!”

“Uh, yes, pup!” Riccolli answered, not bothering to correct his assumption. If anything it could be to his advantage. “And do you know what the smaller one do for the bigger one?”

Max shook his head while Riccoli was undoing his shorts, lowering them down over his black and white boxer briefs. Max could see his stomach when the shirt rode up, and almost moaned seeing that Riccoli had abs.

“Like what you see, eh?” Riccoli teased as he observed the look of awe and interest on the younger boy’s face. Easy didn’t even begin to describe it anymore. He wouldn’t be surprised if the whole gang would have their way with him by the end of the night. He yanked down the front of his shorts, and the thumb sunken into his waistband pulled his underwear along with it. Letting his thin yet lengthy cock fall free. “There, pup!”

“W-woah… that IS big!” Max moaned at the cock. Much bigger than his own, maybe twice his own little cock

“Bet yours look like nothing next to this.” Riccoli said, stroking his cock slow to emphasize his size. “You have my permission to touch it.”

“I-I’m not THAT small!” Max protested weakly. Yet a single hand was gliding up toward Riccoli’s thigh before it reached the base of his cock. He hesitated for a moment, barely brushing against Riccoli’s balls. They were hairy and smelled nothing like Max’s baby smooth skin. More earthy. 

“We’ll see… I’ll be the judge of that.” Riccoli grunted, waiting for Max to really touch him.

With the thought of touching the biggest cock he had ever seen in his head, he mustered all the courage he could gather and finally grabbed Riccoli’s cock at the root. Intense heat, burning lust, pulsed through his small hand the moment Max touched it. It certainly made Riccoli happy judging by the size of his grin. Simpering at Max, lulling him into this.

“Should I show you mine-?” Max asked, about to let go of the length.

Riccoli pulled his cock back and the sudden movement had Max’s grip tightening. He then pushed back into the warm, soft palm. Effectively beginning to fuck Max’s hand. “Nah. You gotta keep doing that, stroking my cock.”

“Oh… why?” Max asked, tilting his head to look around the erect member. It was long and thin, with a darkish pink tip that matched the hairy blond bush at its base. 

“Are you questioning the leader of the pack? We’re the Dog Boys. If I say do something, you don’t question it,” Riccoli snapped, with murmurs of agreement around him. Max was far from the first but by far the easiest among all kids wishing to be a Dog Boy. “So jerk me off!”

Max’s eyes glanced around at the others watching on. Only a few paid any attention to him, watching as the hand pumped along Riccoli’s slim cock. Nervously jerking off his mentor with quite a slow pace which drew a low groan from the blond’s lips. Still rocking his hips to fuck the tender hand in its efforts to please him. Making it quite obvious that Riccoli wanted faster, but Max had little idea what he was doing.

Since Riccoli was moving his hips so much, the younger boy’s hand responded by going faster. Rhythmically moving on its shaft, twisting slightly with each pump.

“Ngh. Not bad, pup… Do this often with yours?” Riccoli asked, going faster into the boy’s small warm hand.

“N-no,” Max, noticing how big Riccoli was, decided to wrap his other hand around it. He always felt better when his whole hand was on the length. “My mom says it will make me go blind, but my eyes are fine!”

“Of course she did. But, you want to do this all the time, right?” Riccoli smirked at the boy’s effort, bucking into him more.

Max’s eyes went a little wider, looking away from him and back at the cock trapped in both hands. Stroking him faster, more intensely to distract and provide more pleasure for the top dog. 

“Mm, now blow it.” The older boy commanded.

“Blow it?” Max looked at the older boy quizzically. His mouth already pursed as he was about to blow some air on the cock.

Watching in confusion, Riccoli slowly raised an eyebrow as cool air blew over the length of his cock. It made him shiver from the surprise cold, so pulled his cock away before it became cold and soft. Confusing Max, who thought he was doing a good job of it. Muttering as his friends chuckled. “What the hell! Put it in your mouth, don’t just blow on it!”

“But that’s what you told me to do!” Max retorted, glossing over the fact that he was just told to swallow the cock.

“Well, do it right!” Riccoli shoved it between the boy’s open lips, which hesitated before closing around his tip. And once more, Max began to blow air on his cock. Truly too innocent for his own good. “Ugh, I want you to suck my cock!”

The older boy rolled his eyes. Max might be eager to do anything, but it might need some lessons first before he could do it properly.

The young skater stared at the glaring cock in front of him. His mind thinking over the order he was just given. To suck on it would mean putting that into his mouth. Not sure if it was truly what he meant, but also unable to think of anything else, the boy finally just shrugged. ‘If that’s what big boys do.’

Seconds later, Max opened his mouth wide. Wider than he had ever done as it slid over the tip of the head, easily going through a couple inches before he finally closed around it. His second taste of Riccoli’s cock, but the first time he took any notice of its flavour, allowing his tongue to swipe at it. He more or less tasted salty, like sweat but there was more to it. Not unpleasant, either as Max didn’t pull away. Instead easing himself down a little more.

There was a tickle in his throat like the boy needed to cough. At a brief glance this should have been easy. He could eat hotdogs just fine, and that was almost the same as Riccoli’s cock.

Riccoli saved him, however, by grabbing the back of his head then guiding Max off. Only leaving the tip inside before he pushed the boy back down. Helping get into a rhythm back and forth, flowing swiftly on the length of his cock.

The older boy was actually pretty impressed at the ease of Max taking his cock. Especially if his confusion was any indicator on his experience.

“Mm, look at him suck, boys!” Riccoli roared over the skating, drawing eyes to Max’s cocksucking as the boy bobbed on his cock. Using that little tongue to daintily flick at its head. Now blushing, of course, when a group of older boys looked at him sucking on the lengthy dick. “Mmm, fuck yeah go faster! Suck my dick like you mean it!”

Not wanting to disappoint with all eyes on him, Max sucked as hard as he could, his tongue licking around as he would on candy.

“Mmm, little longer… faster, pup!” The older boy throbbed as orgasm drew closer. Expressed by hot pulses of his lengthy teenage cock.

Innocent as he was, even he got an inkling on what Riccoli was trying to say. With it being something he learned recently. As he wasn’t ordered to stop, he kept on sucking the older boy’s cock, actually anticipating slightly on what kind of taste he would get. Riccoli moaned something about the boy being hungry for it, but Max’s undivided attention was on sucking the cock. Forcing himself down past his earlier limits, relaxed enough to let it slide down his throat.

“Shit, pup. Here it comes!” Riccoli moaned as he suddenly pushed his length deep into Max’s mouth. His cock pulsing as a hot load started to fill the younger boy’s mouth.

Max yelped in surprise as the taste of cum permeated through his mouth. He couldn’t properly register it however as his mouth was quickly flooded to capacity. With Riccoli having no intention of releasing him, the boy found himself gulping down.

Everyone else could only watch in slight awe as they watched the small boy seemingly handle it with no problem at all.

Shivering at the intense taste of cum, Max could do little more than keep swallowing it. Each steamy hot mouthful of spunk made his eyes recede backwards, turning almost totally white before Riccoli finally pulled him off with a pop. As Max lay there panting, his eyes rolled back into place, staring at Riccoli in a daze.

“You…” He slurred as the last drop rolled down his tongue. “Swear a lot!”

The Dog Boys broke out with laughter. Most boys remarked that cum was disgusting, but here was Max Innocent Reynolds complaining that Riccoli swears.

“That’s just what big boys do.” Riccoli replied as he panted. He felt like he hadn’t cummed for weeks from the boy’s mouth. “I’d say you should try saying fuck or something… but you’re still a pup.”

“Wh-what! But I did the thing!” Max protested, his lips tugging down at the corners.

“Mhm. And you did good, I admit. But that’s not enough.”

Max looked around at everyone, shy of all their grins. He yelped sheepishly when Riccoli started to turn. “Wa-wait! What do you want me to do!”

“Think you can handle more?”

The boy nodded firmly. “Anything!”

“Good. Then strip.”

Already beyond questioning what he should or shouldn’t do, Max fingered the bottom of his hoodie and yanked it off. Throwing it carelessly in contrast to how dearly he held it previously. His shirt followed soon after and he didn’t even pause to take his pants and white briefs off. The Dog Boys has stopped to stare at Max. Watching this small, lithe boy stripping down, revealing his perfect silky body illuminated by the dull lights. His olive chest was hairless and skinny, without definition. That boy’s bubble butt stuck out, but the same could not be said for his little bulge in the front.

Under normal circumstances, he would have been embarrassed to be seen in his tighty whities. But, ignoring that it was the last clean underwear he got, his mind was full of proving himself to be enough of a man for the Dog Boys. Proudly showing himself in the nude just as he had seen Riccoli’s cock. He might not be nowhere near as big as his, but he wasn’t ashamed of it. Standing at maybe three or four inches, a little thicker than a pencil.

Whistling, Riccoli motioned for Max to turn. Watching the boy’s soft butt as he span around showing off the assets they really wanted to see. “Phewwwww look at that ass, boys! I’ve seen girls with worse asses!”

Max wasn’t sure why they were so fixated on his ass, but it sure didn’t sound like an insult. In fact, he was feeling rather admired by it.

“Good thing you lubed me up for the next part. Think he’s ready to be a Dog Boy, fellas?” He got a few grunts in response, some even muttering that he wasn’t quite ready to be a full Dog boy yet. “Whatever dorks, I’m getting some tonight!” 

To show his leadership to the group, the blond Riccoli howled into the night. A few of his top Dogs supported him, howling back while others grunted ignorantly.

Max attempted to howl, but it trailed off in embarrassment.

“We’ll see if we can improve that.” Riccoli smirked, his hand already reaching for the boy’s ass.

The boy jumped as the first hand ever touched his butt. Squeezing it softly. “A-ah! Hey!”

Riccoli’s smirk just widened as he pulled him in, bringing him closer to the ramp. Max didn’t fight it when he got pushed up against the wall, supported by both hands on the smooth stone. Shivering in the buff with cold air gliding over his olive flesh. Until warmth came in the form of Riccoli, who stepped behind him before pressing their bodies intimately close. The older boy proceeded to spit on his palm then work it into his cock while aiming it at Max’s butt.

“O-oh…! This is like that, um, sex stuff Leo talked about! Where the guy grinds on something until he shoots that white stuff… right? Do-doesn’t it need a girl?” Max whimpered, wondering if Leo was somewhat wrong. Naked, check; hard, check; spitting on a cock wasn’t a step. They were just going to grind. Right?

“Nah, just need a hole, like this one.” Riccoli replied, pressing his cock against Max’s butt.

Max gasped and shivered, humped up against the wall. “W-wait you can’t-! I’m a boy!”

“Sshh!” Riccoli assured as he placed a hand on Max’s side to keep him still as he pushed his length in. He loved that sharp gasp as he penetrated the hole, pushing easily past its resistance.

Some had walked to the edges of the park to keep watch for anyone that would break their fun. Others continued to skate without a care even as Max's scream pierced the air. Others still, mostly those that had known Riccoli the longest, were there with their own cock whipped out, beating to it as they watched their leader pound into the boy's sticking ass. He was nice and deep in the Reynolds boy now, holding him up against the skating ramp and easing in.

“Ngggh. Fuck!” Max couldn’t help but swore as Riccoli pushed deeper with each passing second. Sharp pain needling into him and feeling so full from it.

“Look at that ass swallow my cock!” Riccoli shoved in the last little bit, filling Max up to the brim with dick. He grunted and growled, holding it in as the ass adjusted to its first of surely many cocks. He humped a few inches in and out, grinding his hips on Max. “Holy shit. So tight! Gnarly little ass, pup!”

“Y-Yes!” Max exclaimed before letting out a deep moan, not really getting what he was talking about beyond that he got a good ass that hopefully would let him in.

“He’s so into it!” One of the Dog Boys shouted, pumping their cock as Riccoli drilled Max’s tight boy pussy. The way the boy taking it with ease didn’t seem like it was his first time despite everyone knowing otherwise.

Pressing his forehead to the wall, Max hissed. He felt Riccoli’s tip abusing something inside, slamming harder and harder into one spot that was making his cock tense up. Like there was pressure building in his young body. Riccoli was fucking something inside him Max never felt before when jerking off. “Ah! Aaaah! AaaahhHHH! RICCOLI!” 

A moment later his cock throbbed harder than it ever had. A huge watery load of cum shot from the young boy and coated the stone; Each subsequent pounding from Riccoli had another huge rope of the stuff shoot out. Nothing like a normal orgasm. He hadn’t even touched himself yet. Riccoli fucked the cum out of him with that lengthy dick; After all, it was deep and found his prostate pretty easily so Riccoli put all his muscle into it.

The boy’s begging echoed through the park. Pleasure like never before ebbed through his body. Adrenaline pumped into him, much more than the most thrilling trick he was able to pull while skating. 

“Holy shit-! He fucking came!” That alone had Riccoli’s biceps flexing as he pulled Max back by the hips, slamming deeper inside. He pounded him, fucking with no regard for Max himself, grunting huskilky into the boy’s ear. “You’re gonna be all the Dog Boys’ bitch!”

“S-so, am I in?” Max asked in between his gasp and moan as he tried to steady himself.

Riccoli took a while to answer. Too focused on hammering the tight ring to even process the question; To him, Max was just a wanna be skater boy turned fuck hole. “Huh? Sure, whatever… bitch is a female dog, right?”

There were small murmurs of agreement from the crowd, none were really caring beyond wanting to be next into that tightness.

Max himself wasn’t listening much beyond the affirmative ‘sure’, finally howling happily and letting everything loose as Riccoli kept pounding into his prostate.

“Ungh! Here it comes!” Riccoli grunted to his friends with a grin. Max, confused, turned to look at the older boy; his face was scrunched up as he fucked deeper, and it made sense on the next brutal thrust as a flood of cum was emptied into his butt.

“Gahhh” Max let out a deep moan. Wondering if it was any less to the amount he had drunk just earlier.

After a few long moments of grunting and fucking his cum in, Riccoli abrputly pulled away. His breathing was heavy and cock still raging hard, though feeling a little empty now.

“He’s all yours, boys!” He roared as a pair of boys grabbed Max. One shoved into his ass and another down his throat. Max looked surprised and caught in the moment spitroasted between two boys. Riccoli ruffled his hair. “Welcome to the Dog Boys… it’ll be a long night,”


End file.
